期刊
SCIENCE
卷 332, 期 6028, 页码 448-451出版社
AMER ASSOC ADVANCEMENT SCIENCE
DOI: 10.1126/science.1201686
关键词
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资金
- Japan Society for the Promotion of Science
- Grants-in-Aid for Scientific Research [23790012, 23659008, 21550046, 23390006, 23350019] Funding Source: KAKEN
Amination of alkanes has generally required metal catalysts and/or high temperatures. Here we report that simple exposure of a broad range of alkanes to N-triflylimino-lambda(3)-bromane 1 at ambient temperature results in C-H insertion of the nitrogen functionality to afford triflyl-substituted amines in moderate to high yields. Marked selectivity for tertiary over secondary C-H bonds was observed; primary (methyl) C-H bonds were inert. Addition of hexafluoroisopropanol to inhibit decomposition of 1 dramatically improved the C-H amination efficiencies. Second-order kinetics, activation parameters (negative activation entropy), deuterium isotope effects, and theoretical calculations suggest a concerted asynchronous bimolecular transition state for the metal-free C-H amination event.
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